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Solo Traveling the Massachusetts North Shore: Gloucester & Manchester-By-The-Sea

This past November, I took a little solo adventure through the Massachusetts North Shore region. If you'd like to catch up on all the places I visited while on this trip, you can find the links here:


During this trip, I was on a mission to see as much as I could in a very tightly-packed three and a half days. And while I did cover a lot of ground, I will be honest, I didn't see as much of Gloucester and Manchester-By-The-Sea as I would have wanted. I was only in each of these towns for about three hours, so, as you can imagine, I didn't see it all. But, I will say, what I did get to experience, I loved. Manchester-By-The-Sea, especially, really surprised me with its beauty. So for today's post, I don't have a lot of information to share, but I do have some snapshots from some really lovely seaside moments from these two great little towns.



My very first stop this day was Gloucester, and one of the reasons I ended up having to cut my day shorter than expected was because I made a planning mistake that cost me some time. I wanted to visit Annisquam Lighthouse in the very early morning, and left my hotel just before sunrise. I didn't do enough research, and after going out of my way to get there, I came to realize that it's situated on private land and not open to the public. The website I had read said that there was short-term, and very limited parking available to view the exterior of the lighthouse, so I followed those directions, and took a long, slow drive through a somewhat gated community, reading all the signs that said "No lighthouse parking,"  (which the website told me to ignore) only to get to the very end, and not see a single parking spot at all. I was also greeted with lots more "No parking for the lighthouse" signs. Some websites I read about it said the community members don't mind if you park on the street to visit the lighthouse, so long as you're respectful to just go ahead and do it. Other websites reported people getting towed. And since I'm such a rule follower, and because one gentleman was out walking his dog and giving me looks, off I went without seeing the lighthouse because I was convinced I would get thrown in jail or something if I left my car (anxiety disorder problems). So, I was disappointed to have wasted my time, but off I went to my next stop, which was a lot of fun. And made up for a rocky start to the morning.

I spent the rest of my morning at Eastern Point Lighthouse, and I absolutely loved it here. The lighthouse is beautiful, but what I liked the most was the long rock jetty that you can walk down. It was really peaceful here, and a great way to spend a sunny November morning. I was the only tourist there that morning, and the rest of the few others were fishermen, so I pretty much had the whole thing to myself for a couple of hours.










For the rest of my time in Gloucester, I explored the town. I wandered down the Harbor Walk and, of course, visited the Fisherman's Memorial, which is dedicated to local fishermen lost at sea. I also wandered over to the Harbor Loop and walked around Maritime Gloucester, which is a working harbor and museum rolled into one. It's very small, and I didn't go inside because, you know ... COVID. But I did walk around and hang out by the waterfront area a bit, and I loved it. I watched some boats come in and out, and just enjoyed all the sounds of the seagulls and the smell of the sea. I also had the whole thing to myself, which was pretty great.









And honestly, that was it for Gloucester. I had jotted down a local artist's colony to visit, but knew my daylight hours were numbered. What I will say about Gloucester is, if you just follow along the waterfront and keep walking, you can take in so many views of weathered fishing boats, harbors and fishing shacks. So even if you don't have a plan, like me, it was really nice to just wander through an authentic, working maritimes town so easily. 

And next, I was off to Manchester-By-The-Sea to end my last day. 

I actually almost skipped this gorgeous little town because I was getting tired toward the end of my day, and I'm so happy I didn't. I was surprised by its charm, and had the best time roaming the streets at golden hour. 



My first stop was Singing Beach. A couple of people on Instagram reached out/commented that I should stop here. It's known for having a special kind of sand that makes a noice when you scuff your feet against it, and I kind of didn't believe it when I read about it. But guys, it really does make a noise! No, it doesn't sing, exactly, but it does make a squeaking sound that I can only liken to sneakers on a gym floor. I tried to Google why it makes this noise, exactly, but the general consensus seems to be, no one knows for sure. I'm now curious to see if I can get the sands from the Cape to make the same noise this summer.





The beach was insanely gorgeous, too. So much more beautiful than I was anticipating for some reason. Beautiful, clean, soft sand, striking turquoise water, and much longer than I thought it would be. Even in November, there were quite a few people (and dogs) at the beach, so it was nice to park myself in the sand and people/dog watch for a big, and also walk along the shoreline. 

I had no other plans for the rest of my time in Manchester-By-The-Sea, so I ended up parking my car at Masconomo Park because I passed by it on my way to Singing Beach, and made a mental note to come back and walk around for a bit. Then headed into town and wandered some of the side streets until the sun was just about to go down. The first thought I had about the town was that it reminded me just a bit of Nantucket (but, you know, nothing is exactly like Nantucket, so definitely don't have that expectation). The white fences around the water and boat docks just reminded me of when you arrive on Nantucket, and it has an upscale feel that also doesn't take itself too seriously. Mostly, it just felt like a quintessential New England seaside town that you would picture when wanting to visit this region. 













To end my day, I was also surprised by how gorgeous the drive from Manchester-By-The-Sea back to Marblehead was. And once I got home, I was kicking myself for not stopping to take note of where I was, or to snap some quick photos, because I, of course, wasn't at all paying any attention to where I was. All I remember are beautiful stonewall-lined streets and some pull-off's for overlook areas near water views which looked amazing. There were a lot of signs for Essex, too, which is of no help to anyone. But I would love to go back and try to retrace my path someday. As much as I love to extensively plan and research things when I travel, having that little drive without any real idea of exactly where I was, and having the hope of finding it again someday, is actually kind of exciting. 

And that was my last full day on the North Shore. The following day, I visited Newburyport and Plum Island before heading home, and I still also have my day in Salem to recap - coming soon.

What should I do the next time I visit Gloucester or Manchester-By-The-Sea? I'd love to hear some places I missed so I have a reason to go back.






* I traveled to this destination during the COVID-19 pandemic and took all necessary and optional precautions. During the limited traveling I have done during the pandemic, I took the responsibility of not only my own health, but also the health of those around me. I planned excursions and activities that were all outdoors, avoided coming within even 12 feet of another person, relied on take-out at restaurants where I could safety eat outside far from others, or back at my room at the inn where everything had been sanitized and aired-out. Safety during this trip was incredibly important to me, and please know that it was always at the forefront of my mind. 

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